Water → 4'-Formyl-[1,1'-biphenyl]-2-carbonitrile

HRID 1941380Notes

Reaction equation

HRID 1941380 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[CH:5][CH:4]=1.C(=O)(O)[O-:18].[Na+].O>CS(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[CH:5][CH:4]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrileYield 63.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(4-bromomethylphenyl)benzonitrile (12 g) and sodium bicarbonate (26 g) in dimethyl sulfoxide (150 ml) was heated at 120° C. for 5 hours with stirring. After addition of water, the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give crystals. Recrystallization from chloroform-isopropyl ether gave colorless needles (5.77 g, 63%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography on silica gel
  6. customto give crystals
  7. customRecrystallization from chloroform-isopropyl ether

Sources & evidence

ORD record
ord-f6445577e33f4951ac667a278156b4e2
Source dataset
uspto-grants-1997_12
Patent number
US05703110

Reaction notes

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